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Five hundred couch gags, 500 chalkboard punishments, 500 Gracie Films logos appearing after the credits … The Simpsons has certainly surpassed any sensible estimation of success that would have come about at the show’s 1989 premiere. And as the 500th episode sets to debut on Sunday, it’s the perfect opportunity to look back at how it has celebrated its four other “hundredth” episodes.

100 — “Sweet Seymour Skinner’s Baadasssss Song” (April 28, 1994)

Bart’s antics finally have some real-world consequences when his latest prank — unleashing Santa’s Little Helper into the air ducts of Springfield Elementary — gets Principal Skinner fired. Ned Flanders is installed as Skinner’s replacement, but his inability to discipline the students leads to anarchy. Skinner decides to rejoin the Army (this was before the Armin Tamzarian revelations of Season 9), but Bart decides that life is just not the same without his old nemesis and conspires to get him his old job back. This only happens, however, when Flanders references God over the intercom and Superintendent Chalmers fires him in a panic of political correctness. Bart and Skinner seem to come to an understanding, and walk away from each other after a moment of shared respect, only to reveal they have each taped “Kick Me” and “Teach Me” stickers on each other’s backs.

Steve Martin and U2 guest star in this episode where Homer learns a bit about small-town government when he runs for Sanitation Commissioner. He makes big promises, even joining U2 for the classic “The Garbage Man” number, before realizing that his lofty ambitions — 24-hour garbage service, spiffy new uniforms for each sanitation worker — will run through his annual budget in one month. To get more cash, Homer allows other towns to store all their waste in an abandoned mine shaft in Springfield. But that only works till the garbage erupts and spills trash all over town. Homer is fired, and Mayor Quimby decides the only solution is to move Springfield five miles from its current site.

300 — “Barting Over” (Feb. 16, 2003)

Bart discovers that he was once a child star in a series of commercials where he played “Baby Stink-Breath,” which would be bad enough, but he also learns that Homer blew through all his earnings. In his anger, Bart seeks legal emancipation from his parents and receives it. He moves to an apartment building where skateboard legend Tony Hawk also lives, and the two become fast friends. In effort to win back his son’s affections, Homer receives a special skateboard from Hawk that does all the tricks for him, but this soon leads to an all-too-real battle between the two of them. After the dust settles, Homer signs on to star in an impotency drug commercial to help restore Bart’s lost fortune.

When Kent Brockman has a profanity malfunction during a live broadcast — caused by Homer spilling coffee onto his crotch — the newsman is demoted to weatherman and the station fined after morality watchdog Ned Flanders fires off a letter to the FCC. Kent eventually loses his job and ends up sleeping on the Simpsons’ couch (what happened to all his lottery winnings?). The episode then unleashes a daring tirade against media polarization, pointing out the discrepancy between the holier-than-thou Fox News and the edgy primetime programming on FOX. Kent reveals to Lisa that it’s all a conspiracy to funnel money to the Republican Party via the FCC, but before he can follow through on the courage of his convictions and fight the system, the GOP offers Kent his job back with a raise, a proposal he shamelessly accepts.